Enantioselective total synthesis of pyrinodemin A
Authors:
- 10 March 2008
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 6 (8) , 1502-1510
Abstract
Pyrinodemin A 1, a cytotoxic marine alkaloid, was synthesized in a convergent and enantioselective fashion. The key steps are an asymmetric intramolecular dipolar cycloaddition of an oxazoline N-oxide to introduce the bicyclic ring system of the molecule, a cuprate coupling for the extension of the saturated chain and a B-alkyl Suzuki coupling for the introduction of a 3-pyridyl moiety. Reductive amination allowed the coupling of the second side-chain onto the nitrogen atom to give 1. Additionally, attempts to prepare 1 from a trienic precursor by a double B-alkyl Suzuki reaction are described.Keywords
This publication has 26 references indexed in Scilit:
- Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural RevisionMolecules, 2005
- Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar CycloadditionThe Journal of Organic Chemistry, 2003
- Total Synthesis and Assignment of the Double-Bond Position and Absolute Configuration of (−)-Pyrinodemin AOrganic Letters, 2003
- The Suzuki cross-coupling reaction: a powerful tool for the attachment of organometallic ‘NCN’-pincer units to biological scaffoldsJournal of Organometallic Chemistry, 2003
- Design, Synthesis, and 1,3-Dipolar Cycloaddition of (5R)- [and (5S)]-5,6-Dihydro-5-phenyl-2H-1,4-oxazin-2-one N-Oxides as Chiral (E)-Geometry-Fixed α-AlkoxycarbonylnitronesThe Journal of Organic Chemistry, 2000
- Oxazoline-N-oxide mediated asymmetric cycloadditions. Recent progress in the stereo-selective syntheses of β-lactones and β-lactams2000
- Pyrinodemins B-D, Potent Cytotoxic bis-Pyridine Alkaloids from Marine Sponge Amphimedon sp.Chemical and Pharmaceutical Bulletin, 2000
- Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998Journal of Organometallic Chemistry, 1999
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Asymmetric Synthesis. 32. A New Access to Enantiomerically Pure (S)-(-)-Pipecolic Acid and 2- or 6-Alkylated DerivativesThe Journal of Organic Chemistry, 1994